Both the Shulchan Aruch Harav and the Mishnah Brurah use similar terminology when describing the importance of the shin being "pointy" on the bottom and all three branches of the letter shin meeting at a point or "chad" at the bottom of the letter. There is a strong foundation in Halacha for this and for the bottom of the shin to be flat like a moshav (base) is considered questionable (Pri Megadim) and definitely not Kosher Lechatchillah. It is worse if the moshav is very wide, but it is still questionable if it is lechatchillah if there is a thick noticeable base rather than a chad. Even for Sephardim, who lechatchillah make an angular base, it is still important that the base is indeed on a (significant) angle. If the base is flat, even if all three branches of the shin come out of the base connected , as in the top picture, it is problematic. It is worse in the bottom picture below where the right head/ branch comes out of the right part of the base and the m
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